Triphenylphosphine → (R)-5-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}pyrrolidin-2-one

HRID 70519

反応式

HRID 70519 の反応式
[C:1]1([N:7]2[C:11]([SH:12])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][C@@H:34]1[NH:38][C:37](=[O:39])[CH2:36][CH2:35]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.O>[C:1]1([N:7]2[C:11]([S:12][CH2:33][C@@H:34]3[NH:38][C:37](=[O:39])[CH2:36][CH2:35]3)=[N:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinoneHCID 1785279861-phenyltetrazole-5-thiol

生成物 1

HCID 67399039(R)-5-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}pyrrolidin-2-one収率 18.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-Phenyl-1H-tetrazole-5-thiol (9.0 g) and triphenylphosphine (13.2 g) were added to a solution of (R)-(−)-5-(hydroxymethyl)-2-pyrrolidinone (4.5 g) in tetrahydrofuran (90 mL), followed by ice-cooling. A solution of 2.2 M diethyl azodicarboxylate in toluene (23 mL) was added dropwise thereto, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1→1:1→0:1) to give (R)-5-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}pyrrolidin-2-one (1.98 g) as a colorless oil.

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1→1:1→0:1)

出典と根拠

ORDレコード
ord-6e99fe8f850f46e2b4753643d346aefa
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

読み込み中…